The Art of Creating Self-Directed Adventures

Whenever I visit a city, I have a tendency of wanting to go where everyone else isn’t. It’s easy to stay in the downtown areas, complete with visitors’ center signs with the bright yellow “You are here” star on the map. But it’s another thing to wander off entirely, take a random bus line, and see how far it will take me.

I’m currently in Portland, recovering after the 2013 World Domination Summit, a conference full of rather unconventional people (there’ll be a separate post on this later). Having a few extra days, I decided I wasn’t interested in going to the typical tourist spots, depicted in those “official visitors guides” filled with attractions that somebody paid a lot of money to include.

So, what do I need to do this morning? Eat, and get some allergy medicine–because as much as I love these trees, they’re killing my nose! How do I make this interesting? Pick a shop that is as far away and as inconvenient as possible. Why? Because you’re going to see something unusual on the way.

As I took the bus line eastward, I noticed a few (rather obvious) things. The number of Portland food carts lessened, and the number of chain restaurants like Popeye’s and Panda Express grew. (I’m willing to bet Panda doesn’t taste any better in Oregon than in California, where I usually see them.) The buildings in general seemed less well-maintained, and there were more open fields.

Oh look, it’s time to transfer buses. But the bus stop is temporarily closed. What should I do when that happens? Pull out Google maps on your phone! Wait a few seconds for the GPS lock to fixate, but the GPS is not sure what direction you’re facing, so…

Walk randomly! After a block I reorient yourself and head towards the temporary bus stop. I enter, and…


A car slams into a motorcycle right in front of the bus I’m on. It’s a good thing I had no time constraints (that’s kind of the point, isn’t it?), because my bus driver is a witness and is waiting for the police to arrive. At least Portland emergency services are fairly fast, with a police truck and a fire engine arriving within a few minutes. The motorcyclist appears to be shaking it off like nothing happened.

So I finally reach the destination, a small herb shop in the middle of a rather deserted shopping complex. After looking around, I find the thing I’m looking for. After buying it, and praising the Oregon people for their lack of sales tax, I head outside, and continue forward. I originally started on 13th street and am somewhere near 120th.

I find a sandwich shop where I eat a bland, uninspiring sandwich, since there wasn’t anything better around. It’s Arby’s, so I’m not wasting any more sentences on this.

A block away, is a Goodwill mega-store. While there wasn’t anything I was specifically looking for, I wander around inside and think of silly imaginary stories regarding the items they have on sale: “This telescope, it belonged to an amateur astronomer who got so bored waiting for the stars that he started drinking different types of beers. He learned so much about beer that he moved to Eugene to become a brewer, and donated his telescope before moving away.”

I head back. The return trip is always faster since I’m just backtracking along previously visited routes.

Say whatever you like, but I had more fun than sitting in one of those hop-on, hop-off, tourist mega-buses that go along the same routes every day with the overly happy tour guide afflicted with verbal diarrhea.


I did a similar concept in Montreal a few years ago, take the bus line east until to the edge of the river. My friend, who was FROM Montreal, hadn’t even seen that! Whatever the city, the rules never change: Pick a faraway place (or direction) to do your errands, and go. If you normally drive, take the bus or bicycle. Busy downtown areas slowly simmer down into quieter suburbs, and you get to see parts of the city that your average tourist doesn’t.